JCE Software Chemistry Comes Alive!
Diels-Alder Visualization - Part 2 of 3

Animations showing ways in which the shifting bonds in the Diels-Alder reaction can be visualized are presented.

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8.1 MB, 143 seconds

File: MOVIES/DIELS/DIELSB.MOV

Voiceover
Now let's return to the Diels-Alder reaction, focusing on the carbon atom frameworks. The rearrangements of electron pairs between carbon atoms is often represented by an arrow pushing diagram. As the reaction proceeds, these electron pairs are shifted, as drawn here, in a clockwise direction.

The arrows and electron pairs can just as well be drawn circulating in a counterclockwise direction. Although arrow diagrams and chemical structure formulas are drawn as flat two-dimensional figures on the pages of a book, the atomic nuclei are actually moving in three dimensions throughout the reaction.

Here is the starting ethylene molecule, and here is the starting butadiene molecule separated by a large distance. Single and double bonds are gradually shifting and reforming throughout the reaction.

Now let's look at these electron-pair rearrangements from an orbital viewpoint. The three key electron pair orbitals of the starting reagents are the pi bonds of the butadiene and the pi bond of the ethylene. If we represent the electronic rearrangements in terms of the three filled localized molecular orbitals, the bond shifts appear similar to the arrow pushing diagrams seen before.

However we could just as well picture the orbitals as shifting in a counterclockwise direction rather than clockwise.


Creator:  
  Andrew Habermas University of Wisconsin - Madison, Madison, WI 53706
Executive Producers:  
  Frank Weinhold University of Wisconsin - Madison, Madison, WI 53706
  John W. Moore University of Wisconsin - Madison, Madison, WI 53706
Support:  
  National Science Foundation, Directorate for Education and Human Resource
  Institute for Chemical Education University of Wisconsin - Madison, Madison, WI 53706
  Project Seraphim University of Wisconsin - Madison, Madison, WI 53706
Writers:  
  Erica Bode Jacobsen University of Wisconsin - Madison, Madison, WI 53706
  J. Monty Wright University of Wisconsin - Madison, Madison, WI 53706
  Kelly Houston Jetzer University of Wisconsin - Madison, Madison, WI 53706
  Jerrold J. Jacobsen University of Wisconsin - Madison, Madison, WI 53706
Animation:  
  Andrew Habermas University of Wisconsin - Madison, Madison, WI 53706
  J. Monty Wright University of Wisconsin - Madison, Madison, WI 53706
  Jerrold J. Jacobsen University of Wisconsin - Madison, Madison, WI 53706
Video production, editing, and voice:  
  Jerrold J. Jacobsen University of Wisconsin - Madison, Madison, WI 53706
  Greg Minix University of Wisconsin - Madison, College of Engineering, Madison, WI 53706
  Margaret Biddle University of Wisconsin - Madison, Madison, WI 53706